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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Bordetella pertussis [ICD11: XN23B

]

The structure was elucidated in this paper
NCBI PubMed ID: 10899302
Publication DOI: 10.1016/s0014-57930001720-8
Journal NLM ID: 0155157
Publisher: Elsevier
Correspondence: martine.caroff

bbmpc.u-psud.fr
Institutions: Equipe Endotoxines, UMR 8619 du Centre National de la Recherche Scientifique, Biochimie, Universite de Paris- Sud, F-91405, Orsay, France

The endotoxin (lipopolysaccharide) of Bordetella pertussis, the agent of whooping cough, consists of a lipid A linked to a highly branched dodecasaccharide containing several acid and amino sugars. The elucidation of the polysaccharide structure was accomplished by first analyzing the structures of fragments obtained by hydrolysis and nitrous deamination and then piecing the fragments together. The fine structure of the antigenic distal pentasaccharide, presented here, was determined by chemical analyses as well as by high-resolution nuclear magnetic resonance and mass spectrometry. The complete structure was reconstituted and confirmed by matrix-assisted laser desorption/ionization mass spectrometry. The following structure was derived from the combined experimental data:The detailed structure combined with previously reported serological data now allows the synthesis of its epitopes for potential vaccines

structure, Bordetella, Bordetella pertussis, endotoxin, pertussis

Structure type: oligomer
Location inside paper: abstract, Fig. 4
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_115136,IEDB_120354,IEDB_123890,IEDB_130650,IEDB_137340,IEDB_137777,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140630,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_2275071,IEDB_2275073,IEDB_2275074,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, NMR-2D, conformation analysis, GC, b-elimination, Smith degradation, MALDI-MS
Comments, role: lipopolysaccharide, substitution with diphosphoethanolamine is nonstochiometric
3D data: molecular modeling

NCBI Taxonomy refs (TaxIDs): 520
Reference(s) to other database(s): GTC:G68960JL
Show glycosyltransferases

There is only one chemically distinct structure:

CN[C@@H]1[C@H](C)O[C@H](OC[C@H]2O[C@H](O[C@@H]3[C@@H](CO[C@H]4O[C@H](C(=O)O)[C@H](O)[C@H](O)[C@H]4N)O[C@@H](O[C@@H]4[C@@H]([C@@H](O)CO)O[C@H](O[C@@H]5[C@H](OP(=O)(O)OCCN)C[C@](O)(C(=O)O)O[C@@H]5[C@H](O)CO)[C@@H](O)[C@H]4O[C@H]4O[C@H]([C@@H](O)CO[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5N)[C@@H](O)[C@H](O)[C@@H]4O[C@H]4O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@H](N)[C@@H](O)[C@@H]2O[C@H]2O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H](NC(C)=O)[C@@H]1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)[C@H](NC(C)=O)[C@@H]1NC(C)=O

SVG MW SMILES 3D mol Ionize